Cesium carbonate → HCID 89813650, compound

Participants

Reaction Conditions

Reaction Steps

To a nitrogen purged solution of 4-iodo-N-(quinolin-8-yl)benzamide (Intermediate A) (250 mg, 0.66 mmol) in 1,4-dioxane (3 mL) were added cesium carbonate (435.37 mg, 1.33 mmol), xantphos (77.31 mg, 0.13 mmol), Pd2(dba)3 (61.18 mg, 0.06 mmol) and (S)-5,5-dimethyl-4-(o-tolyl)oxazolidin-2-one (164.55 mg, 0.80 mmol). The mixture was purged with nitrogen for 5-10 minutes and then stirred for 3 hours at 100° C. After completion of the reaction (monitored by TLC, TLC system: 30% EtOAc in hexane), the reaction mixture was allowed to cool to ambient temperature and filtered through Celite® brand filter aid. The filtrate was concentrated and purified by column chromatography using silica gel and eluting with 30-40% EtOAc in hexane to afford (S)-4-(5,5-dimethyl-2-oxo-4-(o-tolyl)oxazolidin-3-yl)-N-(quinolin-8-yl)benzamide (80 mg, 26.51%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.55 (s, 1H), 8.95 (dd, J=4.2, 1.6 Hz, 1H), 8.68-8.66 (m, 1H), 8.46 (dd, J=8.3, 1.5 Hz, 1H), 7.97 (d, J=8.8 Hz, 2H), 7.73-7.61 (m, 5H), 7.31 (d, J=7.2 Hz, 1H), 7.23-7.15 (m, 2H), 6.96 (d, J=6.7 Hz, 1H), 5.68 (s, 1H), 1.71 (s, 3H), 0.95 (s, 3H). In CD3OD: the singlet appeared for 3H at δ 2.52 (s, 3H). m/z (ESI) 452.2 (M+H)+.

Provenance & Evidence